This invention relates to herbicidal benzenesulfonamides containing a five or six membered heterocyclic ring consisting of 2-3 heteratoms and 1-2 carbonyl groups as a substituent on benzene, suitable compositions thereof, and their use as agricultural chemicals.
U.S. Pat. Nos. 4,127,405 and 4,169,719 disclose herbicidal benzenesulfonylureas.
European Patent Application (EP-A) No. 83,975 (published July 20, 1983) discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
European Patent Application (EP-A) No. 85,476 (published Aug. 10, 1983) discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA1 C is CO, CR.sub.21 R.sub.22 or SO.sub.2. PA1 E is a single bond, CH.sub.2 or O; PA1 Q is a saturated 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 heteroatoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-2 nitrogen; a 5-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 heteroatoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 1-3 nitrogen and containing one endocyclic double bond; a 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 heteratoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 1-3 nitrogen and containing one or two endocyclic double bonds; or a 5-membered heterocyclic ring, bonded through carbon or nitrogen, containing two adjacent carbonyl groups and 2 heteroatoms selected from the group consisting of 0-1 oxygen, 0-1 sulfur, or 1-2 nitrogen and containing one endocyclic double bond, said Q value may be substituted or unsubstituted wherein the substituent groups are selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.1 -C.sub.3 cyanoalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.3 -C.sub.4 alkylcarbonylalkyl, C.sub.1 -C.sub.4 alkyl substituted with OH or NH.sub.2, C.sub.2 -C.sub.4 alkylaminoalkyl, C.sub.3 -C.sub.4 dialkylaminoalkyl, CH.sub.2 CH(OCH.sub.3).sub.2, ##STR8## C(O)N(CH.sub.3).sub.2, P(O)(OC.sub.1 -C.sub.2 alkyl).sub.2, P(S)(OC.sub.1 -C.sub.2 alkyl).sub.2 or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxycarbonyl; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CH.sub.2 CN, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, CH.sub.2 N.sub.3 or NR.sub.d R.sub.e ; PA1 R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.a and R.sub.b may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R.sub.d and R.sub.e are independently H or C.sub.1 -C.sub.2 alkyl; ##STR9## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR10## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.2 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) when Q contains 2 heteroatoms selected from 0-2 oxygen and 0-2 sulfur, said heteroatoms are not bonded directly to one another, and when Q contains 3 nitrogen heteroatoms, only two of these may be bonded directly together; PA1 (b) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (c) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (d) when J is J-2 or J-3, the substituent Q and the sulfonylurea bridge are on adjacent carbon atoms; PA1 (e) when E is O, then J is J-1 and W is O; PA1 (f) when W is S, then R is H, A is A-1, Z is CH or N and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl; PA1 (g) when the total number of carbons of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two, and the number of carbons of the substituent on Q must be less than or equal to two; PA1 (h) X.sub.4 and Y.sub.4 are not simultaneously Cl; and PA1 (i) when Q is bound through nitrogen and contains 2-heteroatoms and one carbonyl group, and said heteroatoms are bound through the carbonyl, then J is other than J-1. PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.6 ' and R.sub.6 " are independently H or C.sub.1 -C.sub.2 alkyl; and PA1 R.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl or CH.sub.2 CH.dbd.CH.sub.2. PA1 1. Compounds of Formula I where E is a single bond; and Z is CH or N; PA1 2. Compounds of Formula I where E is CH.sub.2, W is O and Z is CH or N; PA1 3. Compounds of Formula I where E is O and Z is CH or N; PA1 4. Compounds of Preferred 1 where Q is Q-1 to Q-30; PA1 5. Compounds of Preferred 4 where PA1 6. Compounds of Preferred 5 where A is A-1; PA1 7. Compounds of Preferred 6 where J is J-1; PA1 8. Compounds of Preferred 6 where J is J-2; PA1 9. Compounds of Preferred 6 where J is J-3; PA1 10. Compounds of Preferred 6 where J is J-4; PA1 11. Compounds of Preferred 6 where J is J-5; PA1 12. Compounds of Preferred 6 where PA1 13. Compounds of Preferred 12 where Q is Q-1; PA1 14. Compounds of Preferred 12 where Q is Q-2; PA1 15. Compounds of Preferred 12 where Q is Q-3; PA1 16. Compounds of Preferred 12 where Q is Q-4; PA1 17. Compounds of Preferred 12 where Q is Q-5; PA1 18. Compounds of Preferred 12 where Q is Q-6; PA1 19. Compounds of Preferred 12 where Q is Q-7; PA1 20. Compounds of Preferred 12 where Q is Q-8; PA1 21. Compounds of Preferred 12 where Q is Q-9; PA1 22. Compounds of Preferred 12 where Q is Q-10; PA1 23. Compounds of Preferred 12 where Q is Q-11; PA1 24. Compounds of Preferred 12 where Q is Q-12; PA1 25. Compounds of Preferred 12 where Q is Q-13; PA1 26. Compounds of Preferred 12 where Q is Q-14; PA1 27. Compounds of Preferred 12 where Q is Q-15; PA1 28. Compounds of Preferred 12 where Q is Q-16; PA1 29. Compounds of Preferred 12 where Q is Q-17; PA1 30. Compounds of Preferred 12 where Q is Q-18; PA1 31. Compounds of Preferred 12 where Q is Q-19; PA1 32. Compounds of Preferred 12 where Q is Q-21; PA1 33. Compounds of Preferred 12 where Q is Q-22; PA1 34. Compounds of Preferred 12 where Q is Q-23; PA1 35. Compounds of Preferred 12 where Q is Q-24; PA1 36. Compounds of Preferred 12 where Q is Q-25; PA1 37. Compounds of Preferred 12 where Q is Q-26; PA1 38. Compounds of Preferred 12 where Q is Q-27; PA1 39. Compounds of Preferred 2 where PA1 40. Compounds of Preferred 3 where PA1 R.sub.8 is C.sub.2 -C.sub.3 alkyl or benzyl. PA1 M is Cl or Br. PA1 L is CH.sub.3, SR.sub.8, NO.sub.2, OH, SO.sub.2 NH.sub.2 or CH.sub.2 SO.sub.2 NH.sub.2 ; PA1 M is Cl, Br, or I; PA1 R.sub.1, R.sub.5 and R.sub.8 are as originally defined; and PA1 R.sub.9 is CH.sub.3 or p-tolyl. PA1 R.sub.1 and M are as previously defined; and PA1 Q is Q-15, Q-16 or Q-17. PA1 R.sub.1, R.sub.5, R.sub.6 and (ii) are as previously defined; and PA1 E is CH.sub.2 or a single bond. PA1 B represents appropriate functional groups, described hereinafter, which may be reacted to prepare o-groups Q-2 to Q-14 or Q-18 to Q-30; and PA1 Q is Q-2 to Q-14 or Q-18 to Q-30. PA1 "The Chemistry of Heterocyclic Compounds," a series published by Interscience Publ., New York and London; PA1 "Pyrimidines", Vol. 16 of the same series by D. J. Brown; PA1 "s-Triazines and Derivatives," Vol. 13 of the same series by E. M. Smolin and L. Rapaport; PA1 F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describes the synthesis of triazines.
South African Patent Application No. 83/8416 (published May 12, 1984) discloses herbicidal benzenesulfonamides of formula ##STR3## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
European Patent Application No. 116,518 (Swiss priority 2/4/83, published 8/22/84) discloses herbicidal sulfonamides of formula ##STR4## wherein X is NR.sub.6 R.sub.7, N(SO.sub.2 R.sub.9).sub.2 or ##STR5## A is CO, SO.sub.2, CONR.sub.23 or CO.sub.2 ; B is C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl; and
U.S. Pat. No. 4,475,944 discloses herbicidal sulfamates, possessing an ortho-heterocyclic ring, such as those of formula ##STR6## wherein W is O, S or NR.sub.1.